Oakland Vacations from $305
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Save 100% on your flight
Price was $732, price is now $492 per person
$492
per person
Feb 25 - Mar 1
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Didn’t have breakfast but I’m sure it would’ve been delicious! Great location, walkable to everything you need from the Acrisure Stadium to area dining & shopping!
Reviewed on Jan 19, 2026
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was $446, price is now $324 per person
$324
per person
Feb 25 - Mar 1
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Staff was extremely kind, friendly and helpful! The space was clean and beautiful! The breakfast was delicious!
Reviewed on Jan 11, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $651, price is now $487 per person
$487
per person
Apr 2 - Apr 5
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.
Reviewed on Jan 14, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Jan 22 to Jan 23
$139 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (576 reviews)
Clean rooms, courteous staff
Reviewed on Jan 13, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $227 total per night from Feb 12 to Feb 13
$227 total
Feb 12 - Feb 13
Total with taxes and fees
9.2/10 Wonderful! (736 reviews)
Yes as to bar. I did not have breakfast.
Reviewed on Jan 11, 2026
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Jan 25 to Jan 26
$139 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (926 reviews)
From reservation to stay everything went really well. Ideal location to highway, restaurants, etc. Room had everything we needed. Loved the kitchenette.
Reviewed on Jan 13, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
4.5/5(48 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
5/5(4 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$65
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$97
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.